On January 6, 2014, iHeartMedia, Inc. (formerly Clear Channel Media and Entertainment; the company which, coincidentally, Sillerman sold the original SFX to in 2000) announced a marketing partnership with SFX, which will see the two firms collaborate on EDM-related content for its digital and terrestrial radio outlets, including a Beatport top 20 countdown show (which will air on some of Clear Channel's major-market contemporary hit radio stations), a national talent search, and an "original live music series" in the style of its Jingle Ball concerts. The partnership expanded upon iHeartMedia's existing EDM-oriented outlets, such as "Evolution", which encompasses a digital radio station on iHeartRadio, and terrestrial outlets in Boston and Miami. iHeartMedia staff, including John Sykes, believed that the deal (particularly the Beatport countdown show) would help provide a higher level of national exposure to current and upcoming EDM artists—its syndication division also produces the "American Top 40".

By August 2015, the value of SFX stock had decreased considerably, going as low as 91 cents per-share. On August 14, 2015, the company failed a takeover bid, initiated by Sillerman, valued at $5.75 a share. According to the "Los Angeles Times", SFX Entertainment is looking into "strategic alternatives" until October 2015 to determine the sale of the company. The company extended its takeover bid deadline in October 2015. In November 2015, Sillerman breached a preferred investment of $30 million into SFX Entertainment. Also in November, Sebastian Solano, founder of SFX's Life in Color brand, was named CEO of ID&T North America and Made Event. On January 13, 2016, the company announced that it had defaulted on a $10.8 million loan after missing a January 3, 2016 interest payment of $3 million. On January 15, 2016, SFX announced that it had received $20 million in new funding.

In January 2013, SFX named Chris Stephenson as its chief marketing officerhe had previously been the CMO of Interscope Records, and is the CEO of fellow Sillerman venture Viggle. SFX also announced a joint venture with the Dutch promoter ID&T with an intent to organize North American eventsID&T previously partnered with Live Nation to hold the first ever American edition of its "Sensation" tour at Barclays Center in Brooklyn. Sillerman also stated in a "Billboard" interview that SFX had acquired New Orleans' Voodoo Experience festival, although it was later discovered that this had not actually occurred (in October 2013, a 51% majority was sold to Live Nation).

In February 2013, SFX acquired Beatport, an online music store specializing in electronic music. In particular, Sillerman felt that the website provided a "massive" platform for both artists and fans to interact; being consistent with his goals for the company. The following month during the Winter Music Conference in Miami, SFX announced that it would acquire a 75% stake in ID&T, and that it would organize a spin-off of its flagship festival "Tomorrowland" known as "TomorrowWorld" in the Atlanta area in September 2013. The company also received a $10 million investment from the communications services and marketing company WPP.

On February 1, 2016, SFX Entertainment filed for chapter 11 bankruptcy. The company planned to restructure as a private entity, and engage in a debt-for-equity swap with its bondholders. Sillerman also stepped down as CEO effective immediately; he will remain chairman and retain his 40% stock interest in the company. Of the situation, he stated that "this expression of confidence from our lenders is testimonial to the vibrancy and potential of our business", and that with the restructuring, "we have the opportunity to achieve all that SFX can and will be." The bankruptcy and transition did not affect any of SFX's festivals, although the fate of the U.S. TomorrowWorld festival (whose 2015 edition was marred by infrastructural problems due to bad weather) was uncertain. The Belgian and Brazilian Tomorrowland festivals are managed directly by ID&T and local partners, and are not affected.

In an interview with "Billboard", Sillerman admitted that there were "no easy answers" surrounding why the company collapsed, but added that he didn't "begrudge the disappointment and anger" of his staff because he was just as disappointed over the company's performance. Former employeea also interviewed by "Billboard" felt that the company did not do enough to leverage its scale, and that the company did not engage in centralization, leading to a lack of coordination between its collection of subsidiaries.

By contrast to the previous SFX, Sillerman intended the new company to be more focused on building relationships and experiences for fans. In response to critics who believed that SFX may "commercialize" the largely underground electronic music industry, Sillerman stated that "if you buy great and successful businesses, you try to empower them to do what they do. And in this case, what they do is provide great entertainment. If you or anyone can ever find an example of someone from SFX telling them how much to charge for a bottle of Cristal at LIV, I'll give you my shares of SFX." Sillerman has emphasized his belief that the live events industry can not be operated in a centralized manner, noting that SFX is "decentralized with full power invested in the entrepreneurs who have made these businesses."

In December 2013, SFX acquired a 75% stake in Paylogic, a European online ticketing company. Paylogic's services are prominently used by ID&T, and were to be phased in across SFX's other event brands over time as deals with other providers (such as Eventbrite and Disco Donnie) expire. Sillerman singled out Paylogic for its ability to handle large "surges" of ticket sales, as had been demonstrated at "TomorrowWorld", the first U.S. event to use the system.

In September 2014, SFX acquired Brazilian promoter Plus Talent, who organize XXXperience and Tomorrowland Brazil. On October 10, 2014, SFX acquired Listn, a Montreal-based startup that developed a mobile app which allowed users to browse their friends' music collections. Listn's employees were reassigned to Beatport, and the service was phased out.

In December 2016, SFX emerged from bankruptcy, reducing its debt by $400 million. Randy Phillips, formerly of AEG Live, was named the company's new CEO. The company was also re-named LiveStyle, with its headquarters re-located to Los Angeles. Phillips felt that SFX as a brand had garnered a negative reputation, and that the company had originally collapsed because it focused too much on growing quickly, performing an IPO, and Sillerman "[selling] a story about sponsorship", which "has to be the icing on the cake - not the cake itself." Phillips also began to describe the company as being oriented towards electronic music in general rather than EDM, and stated that some of their events (such as Mysteryland) will broaden their scope (similarly to the Coachella Festival), but other events will remain predominantly oriented towards electronic music.